


The Reunion

by thatwriterlady



Category: Supernatural
Genre: Arguing, Emotional Hurt, F/M, Fluff and Angst, Frustration, Heartbreak, Lack of Communication, M/M
Language: English
Status: Completed
Published: 2015-02-24
Updated: 2015-02-24
Packaged: 2018-03-14 20:34:33
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 17
Words: 21,375
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3424703
Author URL: https://archiveofourown.org/users/thatwriterlady/pseuds/thatwriterlady
Summary: <blockquote class="userstuff">
              <p>With the 20 year high school reunion coming up for Dean all he can think about is the falling out he had with his best friend Cas at their graduation.  He's debating on whether or not to go.  He'd fallen in love with Cas almost the moment he had met him in their freshman year, but Cas was a playboy with more girls swooning over him than Dean could imagine.  Dean decides to go to the reunion at Charlie's insistance, and face his worst fears.  Will he tell Cas how he feels?</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I know the time frame is off. Don't nitpick! Technically next year would be when Dean would be attending his 20 year. But I wrote it this year, so I tweaked. Deal with it.
> 
> Also, I have a thing for the angst. Cas' playboy nature in this is based on an actual guy I went to high school with. He had girls fawning all over him, and a new one on his arm practically every day. Girls from surrounding schools even knew who he was. He was seen as a player and I made a point of avoiding him like the plague, lol. Not all of my friends were so lucky though. Ran across him years later. He's happily married. And his husband is HOT, lol! Oh, the irony...
> 
> Also, some chapters might be short, but I already wrote the entire thing, just decided to break it into chapters so it's more understandable.

February 2015 

“You can’t be serious.” Dean huffed as he saw the email waiting in his inbox. His daughter Lexi leaned over his shoulder to read the heading. 

“Dad, you’re old. It’s been twenty years now.” She teased and lightly pinched his cheek. He slapped her hand away and looked up at her in annoyance.

“I am not old.”

She laughed and came around the front of the couch to sit down next to him. “Are you gonna go? Maybe that hottie you liked way back when will be there and you two can reconnect.” She raised an eyebrow and leveled him with a smirk that he himself had mastered. Smartass kid. But she was only voicing what he had been thinking. Maybe…

He opened the email and read it, and when he was finished he read it again. His twentieth high school reunion. Had it really been that long? He had avoided his ten year, but this was a big one. Twenty years. Time had really started to fly after graduation, but after he had kids? It was moving faster than a rocket being launched into space. It was being hosted by Lisa, an old friend of his (old girlfriend if he was going to be honest with himself), and Charlie who had been one of his best friends back in the day. He hadn’t seen her in years. There was a link to a Facebook page where details for the reunion were going to be listed. So many people he had lost touch with over the years, and sure, there were people he was eager to see again, but one name stood out from the rest. One person he wanted to see above and beyond anyone else, even at the expense of his heart being broken all over again. The one person that would be the reason he would even consider going in the first place. Castiel. He looked over at his daughter who was busy texting someone on her phone. Kids today. They didn’t know what it was like to live before the time of internet and smartphones. Back when you had to actually pick up a phone to call someone, and then pray their parents weren’t the one to answer, or passing notes in class to tell the person you liked how you really felt, or to share gossip with friends.

“Hey kiddo, is it hard to set up a Facebook account?” He asked. His daughter looked up at him, her expression a mixture of surprise and amusement. “No, not really, why, do you want to set one up?”

He pointed toward the email. “They’re putting all the details on there, so I suppose I need one so I can follow along with the plans.” He ignored the smug smile she gave him. “I knew you couldn’t resist.” She said as she moved closer and leaned over him to open a new browser tab. In less than ten minutes she had an account set up for him. She even established a profile picture for him and added herself as his first friend. 

“So now what? How do I find that page?” He asked, suddenly feeling very old. She moved back to his email and clicked the link that had been given and joined the page. “It’s that simple dad.” He thanked her as he began scrolling down the page, reading the posts from people that were already planning to go. Of course he was looking for one name in particular. But people were reaching out, finding other long lost classmates and letting them know about the reunion, so maybe this time Castiel would get the message, and maybe he would come. With a fond smile he remembered his old friend, and he felt an ache in his chest suddenly, a reminder of how deeply in love he had fallen with that blue eyed boy.


	2. When First They Meet

**Summary for the Chapter:**

> The first time Dean meets Cas.

September 1991

Dean was lost. That was a given. The way these halls were marked was confusing and a last minute schedule change meant he was supposed to now go to English in A Hall instead of math in M Hall. Except none of these halls were marked as A. As people hurried past he stood there staring dumbly down at his schedule and feeling stressed out way more than he needed to be on his first day of high school. 

“Are you lost?” A voice suddenly asked. Dean lifted his head and turned to find himself facing a boy with messy black hair and bright blue eyes. “Oh, they changed my schedule and I can’t find A Hall. Do you know where it is?” The boy smiled and Dean was momentarily stunned by the it. The boy was beautiful. He held out his arms. “You’re standing in A Hall.” Dean felt the blush rising in his cheeks and he willed it away. “Oh, I didn’t realize this hall had a letter too.” He said, and felt stupid for saying it. The boy dropped his arms and moved closer, taking Dean’s schedule from his hands. “Oh, you’re in advanced English right now? Me too. Come on, we can walk together.”

He handed Dean back his schedule and they started walking. “I’m Dean.” He told the dark haired boy. The boy seemed to be looking him over, a pleasant smile still on his lips. “I’m Castiel.” Dean raised an eyebrow.

“Castiel? That’s a mouthful.” He remarked. Castiel just shrugged. “Perhaps when people actually use it, but most people just call me Cas.” Dean grinned. “It’s nice to meet you Cas.” Cas grinned back. “It’s very nice to meet you too Dean.”

**Notes for the Chapter:**

> All chapters will be posted today. Leave kudos if you like it.


	3. The Wonderful World of Facebook

**Summary for the Chapter:**

> This is an AU. In this world Dean is NOT tech savvy. Deal with it, lol.

February 2015

Lisa had contacted Dean directly, almost the moment he had joined Facebook, and immediately private messaged him to ask him how he had been and what he had been up to. Lexi had to explain the private messaging but he got the hang of it pretty quick, and he shooed her away so she couldn’t read his exchanges with Lisa. She of course wanted to know if he was married, if he had kids, what he was doing now, and he wished he could have been standing face to face with her when he gave her the answers she sought out. No, he was not married, he was divorced, he had two kids, Lexi who was nineteen and Connor who was seventeen, and he was a teacher. The part he wished he could see her expression was when he mentioned his ex-husband. She hadn’t immediately responded when he’d said that, and he could only imagine how her mind must be reeling. It was a drastic change from the Dean Winchester she’d known so long ago. Of course then came the super nosey questions, like was he gay and was he seeing anyone. He quickly told her that if she was fishing, she was using the wrong bait. Her flirty responses became more clinical and after a few more messages she seemed to drop off the face of the planet. It had amused him nonetheless to turn her away for the second time in twenty years. He wasn’t gay, he was bi, but he wasn’t interested in her. He hadn’t even really been interested in her when they’d dated. She was just a pretty face back then with a hot body, and she had been nice to him. So for a couple of months they dated, but when she pressed for sex, he broke up with her. Dating was one thing, sex was something else entirely, and he hadn’t wanted it with her. As the week progressed he found that he had a lot of friend requests from former classmates, and he was able to reconnect with people he had truly missed over the years. Charlie found him almost immediately and sent him a request. Within ten minutes of him accepting her request she was pm’ing him and demanding his phone number. He gave it and she called right then, and it was like the last twenty years had never happened.

“Dean! Oh my God! I have missed you so much!” She cried in his ear as soon as he answered his phone. He couldn’t help but smile.

“I missed you too. What the hell happened to you? You just disappeared and I couldn’t call you anymore. Your mom disappeared too. I couldn’t find you. Not cool Charlie.” He chastised.

“I’m so sorry! I did something kind of awful, but it turned out to be good in the long run. I was starting into hacking back then and I kind of got caught. It worked out in the end though, I work for the NSA now.” She explained.

“What? No way!” 

“Yep. I’m one of their top computer programmers, but that’s not all I do.” She said with a laugh. He had always known that she would end up working with computers.

“So Dean! Tell me everything! Did you ever marry Castiel? I know you lusted after him for like forever!” She asked.

“Uh, no. He never knew how I felt and we lost touch after graduation.. I did marry a man though. Scott. But we’re divorced now. He was a cheating bastard. I’m not seeing anyone now. I have two kids, Lexi and Connor from a relationship I had right out of high school. Oh, and I teach high school English, AP English Lit to be exact.”

She gasped. “You actually married a man?! And you couldn’t tell Cas how you felt about him? I’m so disappointed!”

“Yeah, I did a lot of soul searching and a lot of growing up after high school.” He admitted.

“Well, you’ll be happy to know that I know exactly where Cas is, and what he’s been up to. How do you think I got your email? I emailed him too. He emailed me back directly a couple of days ago. Asked about you actually.” There was no hiding the smug tone in her voice, and the thought of Cas asking about him made his heart start to race.

“Really? He asked about me?” He could hardly believe it! Their last words had not been friendly ones and the idea that after twenty years Cas still wanted to know how he was excited him.

“Yes Dean, and I kind of told him you were coming to the reunion. He said he might come this time. Please tell me I didn’t lie to him!” She cried, and it made him laugh.

“Oh, I’m coming, you can count on that.” He told her. If there was even a slim chance Cas was going to be there, he was definitely going.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it, leave a kudos and a comment.


	4. The Crush

**Summary for the Chapter:**

> Dean realizes he has a crush on his best friend.

September 1991

Dean learned that he had three classes with Cas as well as lunch, and for some odd reason he really liked the guy. He was a scrawny little thing dressed in polo shirts and faded jeans, and his hair never seemed to be brushed, but he was smart with a quick wit and a sarcastic nature that Dean really liked, and they hit it off immediately. Before the month was out they were practically inseparable. While Dean made plenty of friends, Charlie, Benny, Viktor, Robin, there was no one that he enjoyed spending time with more than Cas. They studied together and on weekends they hung out watching movies or playing video games. By the start of October Dean realized he had a crush on his friend, and that only served to confuse him. Cas, however, seemed to be oblivious and when he started dating a girl named April, Dean couldn’t help but be jealous. He just didn’t understand why he was jealous since he knew he liked girls. Charlie, always the observant one found him sulking one afternoon after he had left Cas and April alone in the back hall after they had started making out. He wanted Cas’ lips on his, not on that girl’s, and he was confused and angry over the entire situation. When Charlie happened upon him he was sitting on one of the bleachers out by the football field.

“Winchester, what are you doing out here? It’s cold as hell!” She sat down next to him and leaned forward to get a good look at his face.

“Uh oh, what’s her name?” She asked.

He looked over at her, a deep scowl on his face. “What?”

“Your face tells me that someone just broke your heart. I just want to know her name.” She said.

Dean lowered his gaze to his hands which was practically wringing in his lap. Charlie sat back but he knew she was watching him, waiting for him to say something to her.

“It’s not a girl.” He finally said, though the words were spoken so softly that she barely missed them. “Oh….”

He looked up sharply and she could see the fear and distress in his eyes. “Please don’t tell anyone! I don’t even know why I’m feeling this way. I don’t understand it.” She placed a reassuring hand on his arm.

“Dean, I’m not telling anyone anything. It’s none of their business anyway.” He relaxed a bit under her touch, lowering his eyes once more to his hands. “He clearly doesn’t like me like that anyway, and I’m not sure I’d know what to do if he did.”

Charlie moved closer to rest her head on his shoulder. “Is it Cas?” She asked.

Reluctantly he nodded. “Yeah.”

“He is a bit of a flirt, isn’t he. I don’t think he’s serious about April though.” She said.

“Doesn’t matter if he is or not, he’s into girls. Hell, I’m into girls. I don’t get why I’m feeling like this.” He groaned and leaned his head against hers.

“Have you liked other boys before? Like, thought they were cute or that you’d like to kiss them?” She asked.

He thought about that question for a long moment. There had been the cute boy at the movie theater that worked the popcorn machine, and there was his neighbor Xavier across the street… “Yeah, I’ve liked other guys, but not like this.” He finally admitted.

“But you like girls too?” She asked. He didn’t hesitate to answer this time. “Hell yes I like them.” She giggled and lifted her head to look at him. “Dean, you’re bisexual. It’s perfectly normal, and don’t let anyone ever tell you otherwise.”

“What does that even mean?” He asked. He thought maybe he had heard the term somewhere before, but he wasn’t sure.

“It means you like boys and girls, though in your case maybe you like the girls a bit more?”

He shrugged. “I haven’t dated anyone before so I wouldn’t know what I like more. I just know I like boobs.” 

Charlie laughed at that. “I’m going to let you in on a little secret Dean, I like boobs too.” She gave him a wink and laughed when his eyes widened in surprised.

“You’re…what, a lesbian? Or are you bisexual too?” He asked. “No, I’m a lesbian. I only like girls.” She explained. He nodded. That he understood, he had an aunt who was a lesbian. Well, technically two aunts…

“So get out there and date. Find some pretty girl or guy to grope in the dark and get your mind off Cas. You’ll be glad you did.” She told him. Her advice had not let him down thus far so he decided to heed it this time. “You’re right. I’ll find someone. Just watch.”

They got up and went back inside. Cas and April were still tucked into the same doorway when they walked in and Cas turned to look at them, that beautiful smile Dean had come to love seeing plastered across his face. He ran a hand through his hair and stepped away from a very flustered looking April to walk over to him and Charlie. 

“Where were you guys?” He asked, noting the flush in Dean’s cheeks. 

“Sitting out on the bleachers.” Dean replied. He was surprised that Cas looked cool and collected, unlike his girlfriend.

“We still going back to your house?” Cas asked. Dean shrugged. “Unless you and April had plans.” 

Cas shook his head. “Nah, we don’t. Come on, I need to play a few rounds of Legend.” He started walking, leaving a disgruntled and rather abandoned looking April behind. Dean glanced over at Charlie who just shrugged. She couldn’t make heads or tails either of what Cas and April had together. He hurried to catch up to his friend, resisting the urge to capture his hand and hold it. It was going to be a very long four years of school if he never was able to tell Cas how he really felt.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	5. Charlie Comes to Visit

**Summary for the Chapter:**

> Charlie can't wait until the reunion to see her former best friend, so she pops in for a visit.

March 2015

Charlie came to visit. Dean was thrilled to see her and welcomed her into his house with open arms, and she hugged him so tight she took his breath away. He led her into the kitchen where he grabbed a couple of beers, offering her one. She took it and finished half of it off in one big gulp.

“How was your flight?” He asked as he sat down at the kitchen table across from her.

“It was good. Of course my wife couldn’t figure out why I needed to suddenly pick up and leave to come see you, but well, she didn’t go to school with us and she has no idea how awesome we are together.” She replied with a wink. He laughed and shook his head.

“You look good Dean. You really grew up.” She told him.

“And you still have the reddest hair of anyone I know.” He teased. She laughed at that.

For the next hour they talked about old times, old girlfriends, and he told her about Lisa the month before. She shook her head and snorted when he told her how nosey Lisa had been. “She always had it bad for you, but I knew you didn’t like her nearly as much as she liked you.”

Dean nodded and sipped at his beer. “She slept with most of our senior class.” 

“I know. About the only ones she didn’t sleep with were you and Cas.” She remarked.

“I’m not so sure she didn’t get into Cas’ pants.” He joked, but it hurt him to even utter the words.

“No, she didn’t sleep with him. As a matter of fact I don’t think he slept with any girls in high school.” Charlie told him.

Dean frowned. “I was friends with the guy all four years. He was getting more tail than the entire football team put together. He had to have dated nearly every girl in our grade, and then a bunch more in the grades under us.”

Charlie smiled around her bottle of beer. She took a sip and set it back down on the table. “We girls, we talked. I was friends with more than a handful of the girls he dated, and you’d be surprised to learn that he actually didn’t sleep with any of them. Not that they didn’t want to, since he had earned himself a reputation as a Casanova of sorts, but I heard from more than one girl that as soon as they pushed for sex, he dumped them. I don’t know what he was telling you but the girls were telling a completely different story.”

Dean frowned. “I can’t believe it, he was lying to me? He bragged all the time about the different girls he slept with! It got to the point where I actually couldn’t stomach listening to it anymore. It hurt too much to hear it.”

She reached across the table to squeeze his hand. “I know he spent most of high school being a rather shitty friend to you. I never did understand why you even bothered to stay friends with him, or why you liked him so damn much.”

Dean closed his eyes, remembering a Castiel that was so much more different than the one that most people saw.


	6. Cas' Christmas Gift to Dean

**Summary for the Chapter:**

> Cas proves that he listens to his friend when Christmas rolls around and he gives him the one gift Dean never would have asked for for himself.

December 1991

“Dean, this is for you.” Cas was standing on his front porch holding out a gift wrapped box, that beautiful smile on his face. His cheeks were rosy from the cold and looked just so damn kissable that it took every ounce of willpower not to just grab him and do exactly that. Instead Dean took the box and motioned for Cas to come in the house. 

“It’s still three days until Christmas you know.” Dean said with a laugh as he watched Cas take off his coat and hat and hang them on the hook by the door. Cas was smiling again. “I know, but tomorrow we’re leaving for my aunt’s house, so I won’t be back until the 26th. I wanted to give you your gift now.” Cas explained.

Dean hugged the box a little tighter. “Gee, thanks. I have yours too, it’s in my room. Come on.” He headed up to his room with Cas right on his heels. Once inside he closed the door and watched as Cas threw himself back on the bed, just making himself at home as he usually did. Dean set the box on his desk and went to his closet to get the gift he had bought for Cas. He had put a lot of time and effort into choosing it and he found that he was nervous now at the idea of actually giving it to him. Cas was sitting up, watching him, an excited look in his eyes that seemed to make his already bright blue even brighter. At least he’d had the chance to wrap it. He pulled it from the closet and handed it over. It didn’t take a genius to realize it was a record, but that didn’t hamper Cas’ excitement at all. He accepted the gift and looked up at Dean. “Let’s open them together.” Dean nodded and grabbed the box off his desk, carrying it over to the bed so he could sit down next to his friend. As Cas started to tear the paper off his gift Dean did the same with his. 

 

“Oh, yes!” Cas exclaimed as he held up the record to examine the cover. Dean had never seen him so happy before. “Dean, how did you know I wanted this one?” He turned those blue eyes on him and Dean was pretty sure his heart had just stopped for a second. “You said they were your favorite, and last time I was at your house I took a peek at your records to make sure you didn’t have that one.” Cas smile grew brighter. “Thank you, I love it. I can’t wait to listen to it.” He looked down at the box in Dean’s hand which was still only half unwrapped. 

“Come on, open it!” 

Dean smiled and tore off the rest of the paper. The lid had been taped down and after peeling back the tape he was able to lift the lid. His eyebrows went up as he pulled out a package of guitar pics. “This big box just for this?” He asked as he plucked the package from the box. “I don’t even have a guitar man. I told you that.” Dean was thankful for the gift but it felt a bit thoughtless. Cas knew he didn’t have a guitar and that his parents couldn’t afford one.

“Yes you do.” Cas said.

Dean cocked an eyebrow up at him. “No, I don’t, you know that.”

“You have one.” Cas insisted, and then he was on his feet and out the door. “Wait there!” He yelled, and Dean could hear the sound of feet as they raced down the steps. It was almost a full two minutes before Cas returned, and there was no hiding the look of absolute shock on his face when Cas handed him a guitar.

“I know you had your heart set on an electric one, but this was the best I could do.” If Dean was right, Cas was actually blushing right now.

Dean ran his hands down the side of the instrument and looked up at his friend with awe and shock. “How…when…” He couldn’t quite form the question he wanted to ask. Cas sat down next to him again. “You said you really wanted to learn, so I saved up to buy my brother’s. He stopped playing a long time ago and he barely played at all in the first place. I knew how much you wanted a guitar of your own.” Cas’ response was definitely shy, and again Dean fought the overwhelming urge to kiss him.

“I don’t know what to say man. Thank you. This might be the best gift I’ve ever received.” And Dean meant that. No one had listened to him like Cas did, and actually cared enough to want to fulfill one of his dreams. Cas was practically beaming at him.

“I can’t wait to hear you play something on it.”

Dean laughed and tried a few notes of a song his dad had once tried to teach him. It came out flat and made him cringe, but he was determined to learn how to play that and many other songs. Cas looked way more excited than he did and it helped to raise Dean’s mood even more. Any moment spent alone with Cas was pure heaven.

“Thank you Cas, I really mean that.” He said and Cas’ smile brightened further.

“Anything for you Dean, you’re my best friend.”

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	7. Dean Gets a Text

**Summary for the Chapter:**

> Dean reconnects with one of his old friends from high school, Benny.

April 2015

Charlie’s visit was brief but she made sure he knew everything was planned for the reunion, and she promised to keep in touch. He was pretty sure that now that she was back in his life, she wasn’t going anywhere. Life went on as usual, it was only April after all and the school year wasn’t over yet and he had his job to focus on, though he found his thoughts turning more and more to Cas. He wondered where he was, what he was doing, if he was married… That last thought he tried to shake from his mind but it wouldn’t leave. Why wouldn’t Cas be married? He was gorgeous, enigmatic, and a flirt. Of course he’d have caught some beautiful woman’s eye and had probably been settled down for years, so really, there was no reason to be so excited to finally see Cas again after all these years, but still, he couldn’t help himself. What he couldn’t figure out was why he still cared after all this time. 

It was the last Friday of the month and he had just given an assignment for a paper on Hamlet when he felt his phone vibrate in his pocket. Normally he didn’t check his phone during school hours but everyone that had his number knew he wasn’t available until after two thirty, so his first thought was that something had happened to one of his kids. He pulled the phone from his pocket and keeping it under his desk, opened the message.

Unknown Number: Hey stranger!

Dean frowned. Who the heck was this? He had a momentary debate over whether he should answer or not. Curiosity finally got the better of him though and he typed back a response.

Dean: Who is this?

He stuffed the phone back in his pocket in order to pay attention to his students and a few minutes later he felt his phone vibrate again, but this time he ignored it. This was his last class anyway, he could answer once the bell rang. His attention was distracted by questions about the essay, and the talk turned to views on Hamlet’s reaction to his father’s death and how it applied to modern times, and before he knew it the bell was ringing. Dean watched his students file out of the class, smiling and bidding him a nice weekend as they went. Once the last student was gone he pulled his phone from his pocket and checked. Sure enough, there was a new message.

Unknown Number: It’s Benny man! I got your number from Charlie! How have you been man?

Dean smiled and quickly added Benny’s number to his contact list before responding back.

Dean: Hey! I’m good! How are you?

Benny: I’m great! Can you believe we’ve been out of school twenty years this year? Man that’s insane! What have you been up to? Are you still in Lafayette?

Dean: It’s crazy, it doesn’t feel like twenty years. I’ve been busy. Did the whole family thing. I’m a teacher, you texted me during my last class, that’s why it took me a bit to respond. I am not in Lafayette anymore, got out about twelve years ago. I’m in Chicago now. What about you?

Benny: Oh man, I’m sorry, I wasn’t even thinking! I’ll keep that in mind though. I’m good. I did the whole family thing too. Married my college sweetheart Andrea. We have four kids and one on the way. I’m an electrical engineer. We’re not far from you though, we live in Palatine. We should totally get together, bring the families to meet.

Dean: It’s just me and my kids but yeah, totally. Four kids? Almost five? You used to swear you’d never settle down. I find that ironic.

Benny: Yeah, well, some people change. Can you believe Charlie finally got married? She’s one I never expected to settle down.

Dean: I know, but from what I hear her wife is fantastic and keeps her grounded. I look forward to meeting her at the reunion. You’re going, right? I think I’m bringing my daughter Lexi with me so I don’t have to go alone.

Benny: Of course I’m going. Bringing Andrea with me. Her sister’s going to watch the kids for us that weekend. I’m excited to see everyone again. It’s been too long.

Dean: Same here. A lot of people I lost touch with that I wish I hadn’t.

Benny: Like Cas?

Dean: Yeah, like Cas. And like you and Charlie and Ash, and I could keep going. I literally lost touch with everyone after I joined the Army.

Benny: You have a lot of catching up to do.

Dean: That’s an understatement!

The texting went on, back and forth, with plans to meet up the following weekend. The reunion wasn’t scheduled until the second week in June but Dean was eager to see his old friend before then. It was the weekend that he would have Connor, and Benny had a fifteen year old son, so he hoped the boys would hit it off. Lexi lived wherever she felt like, and lately she felt like living at Dean’s. He was ok with that. He never had liked living alone. When he got home he found his daughter stretched out on the couch with her psychology book open, taking notes. He was so proud of her for getting into UIC on a full scholarship. He often thought she took more after his brother Sam than she did after him. She looked up and smiled when he walked in.

“Hey princess.” He said.

“Hey dad.”

“You want to go out for dinner tonight or should I just make some burgers or something?” He asked as he stripped out of his coat and hung it up.

“Definitely go out, I feel cooped up here.” She replied, sitting up and closing her book.

“Ok, let me check my emails and change. I don’t have papers to grade today, but I will Monday.” He sighed as he started for his room. She didn’t respond and once he was alone in his room he stripped out of his dress shirt and pants, opting for a tee shirt and jeans. He went to his desk and turned on his computer and while it booted up he put on his socks and his boots. Once the sign in screen popped up he logged on and went straight to his emails. 

There was mostly junk, but his brother had emailed him pictures of the baby and he stopped to look at them. It was hard to believe Sammy was all grown up with a family of his own. He had just become a father last September and his son Danny was the spitting image of Sam when he was little. Dean found himself wishing his brother wasn’t clear out in California. He hadn’t gotten to meet the baby yet and he was eager for his trip at the end of summer to finally go and meet the little rugrat. Moving on from the pictures there really was nothing else of interest so he closed his emails out and turned the computer off. When he returned to the living room Lexi was pulling her shoes on.

“What are you in the mood for?” He asked. She shrugged. “Anything but Chinese, we had that last week.”

He grabbed his coat and put it on. Lexi joined him at the door. “Ok, let’s go get food.”

They decided on American food in the end and as they settled into the booth they were directed to Dean took a moment to look around. It was fairly busy for a Friday night and it was buzzing with activity. A woman sitting at a booth across the aisle with several other women caught his eye and she smiled at him. He smiled back. 

“Flirting again dad?” Lexi teased. He rolled his eyes and turned to look at his daughter. “I’m not dead.” She laughed and looked over at the woman before looking back at her dad. “But what about-” He held up a hand to stop her before she could finish the sentence. He suddenly wished he didn’t have such an open relationship with his kids. Lexi knew all about Cas, and how he had pined after him for four long years only to have Cas blow up at him in the end and break his heart.

“No Lex, that ship sailed twenty years ago. At this point if I could just reconnect and be friends with him again I’d be happy, but I’m smart enough to know there would never be anything more than that. He’s straight, remember?” Reluctantly she closed her mouth and nodded, but seeing the sad, defeated look in her dad’s eyes every time he even so much as thought about Cas ate at her. She wouldn’t push it though, it was a painful subject. Instead they ordered their food and Dean deliberately avoided making eye contact with the woman across the aisle. Any interest he’d had was now gone.


	8. A Homecoming Date for Dean

**Summary for the Chapter:**

> Cas learns that Dean has a girlfriend, and that he's taking her to homecoming.

August 1992

Dean was ready for this. They were sophomores now. That meant no more rude comments in the halls and a stop to the upperclassmen trying to shove him into lockers. Of course he didn’t fit, he was too tall and too broad in the shoulders, but that didn’t mean they hadn’t tried. And poor Cas, he was just thin enough and just small enough to get shoved into his locker and for the door to get shut. It was a miracle that the guy wasn’t completely claustrophobic by now. 

Sophomore year was starting out good for both of them. While Dean still wished Cas would look at him the same way he looked at Cas, he had been noticing a couple of girls, and one in particular seemed to be interested in him too. When he started dating Tess they kept things quiet, unlike Cas and his many conquests. It was almost two months into their relationship and time for the homecoming dance before Cas learned about Tess. They were sitting in Dean’s bedroom doing homework and talking when the subject of the dance came up. 

“We should totally go together. Get a bunch of guys together and go, you know?” Cas lifted his head to look at Dean, to see what he thought of that idea.

“I thought you had a date?” Dean asked, looking over at his friend who was sprawled across the bed on his stomach. Cas shrugged. “I never asked anyone.”

Dean looked down at his notebook but he was still thinking. Cas had his choice of girls, all of them were throwing themselves at him, so why didn’t he want to take one of them?

“So should we call up Ash and Benny and the rest of the guys?” Cas was still watching him.

“Uh, you’ll have to count me out.” Dean said, still not looking up. Cas frowned. “Don’t tell me you’re not going.”

Dean shook his head. “No, I, uh, have a date.”

Cas’ eyes widened for a second before narrowing as he sat up on the bed. “You have a date? Who?”

“Tess Michaels. I’ve sort of been seeing her for a couple of months now.” Dean admitted. He couldn’t help the blush that rose in his cheeks and burned clear up to his ears. For a long time Cas was quiet. “I didn’t know. I didn’t see you guys together in school.”

“I don’t- We’re not really into the whole kissing in school thing.” Dean said quietly. He could still feel those blue eyes watching him and when he looked up he swore he saw hurt in them. “You like her?” Cas asked. Dean gave a small nod. “She’s nice, and she’s pretty.” ‘She’s not you though’ he thought with a internal sigh. Cas nodded and laid back down, his attention back on the book in front of him. It was almost another twenty minutes before he spoke again.

“I’m just surprised you didn’t tell me you had a girlfriend. I always tell you about whoever I’m seeing.” 

Dean looked up again. “Sorry.” Cas looked up and smiled, though it was tight. “It’s no problem. But you like her enough to take her to the dance?” Again Dean shrugged. “She asked me.”

“So….if someone else had asked, you’d have said yes?” Cas asked. “Maybe. If the right person asked.” Dean leveled his friend with a gaze that Cas was making no effort to look away from, and he wasn’t exactly sure what to make of that. It was Dean that had to finally look away. That was way too intense, and so far had been the closest he had ever come to telling his friend that he liked him. They returned to their homework and the dance wasn’t mentioned again. Cas ended up not going.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	9. Dean Gets Cold Feet About Going

**Summary for the Chapter:**

> Dean decides he'd rather stay home than risk learning that Cas is happily married with a family, but Charlie isn't letting him back out of it.

May 2015

Since Benny had sent him a text last month they had talked regularly and gotten together several times. This particular weekend Benny was coming to the city so they could attend a Cubs game. Dean was excited since he had to practically drag Connor to any kind of sporting event. When Benny showed up at the house Dean couldn’t keep the huge grin off his face. He hugged his friend and welcomed him into his house.  
“Nice place you got here man.” Benny said as he stepped inside and looked around. “Thanks. It’s humble, but it’s home.” Dean said. “Want a beer or do you just want to wait until we get to the park?”

“I’ll wait for the $12 beers.” Benny said with a laugh. Dean smiled and nodded. “Yeah, I don’t exactly want to drive through traffic with a buzz.” Benny moved to a picture sitting on the table next to the couch and picked it up. “This is your daughter’s high school graduation?” Dean nodded. “Yep. She was valedictorian.” Benny pointed to the man on the other side of Dean’s daughter. He was smiling with his arm around the girl too. “Who’s the guy with you?” Dean glanced up at him and then at the picture. “My ex-husband, Scott.” Benny couldn’t hide the surprise on his face. “You were married to a guy?”

Dean glanced at the frame his friend was holding. “Yeah, but he was a cheating asshole. We divorced last year.” Benny set the picture back on the table. “You never said you were married to a guy.”

Dean was busy sending a text to Lexi telling him he wasn’t going to be home when she got back from classes but he paused to look up. “Does it make a difference?” Benny shook his head. “Nah, not at all. I figured it out back in the day that you swung both ways. I was just surprised. I knew you had a thing back in the day for Cas. Always expected you to end up with him. Not with whoever this douche nozzle is that cheated on you. How long were you even married?”

Dean finished the text and sent it before pocketing his phone. “We were together for almost fourteen years, married for seven of them.” Benny clapped him on the arm and smiled wide. “Well it’s his loss. Come on, let’s go enjoy some baseball man.”

The game was the relaxing distraction that Dean needed, and he’d forgotten just how much fun it was to hang out with Benny and by the end of the game they were in good spirits. When Benny finally left to make the drive home Dean was still smiling. He hadn’t been to a game in ages, and to make it even better, the Cubs had won. It was the best game he’d seen in years. When he walked in the front door Lexi was sitting on the couch watching TV. She smiled when she saw his face, saw how happy he was. “You had a good time?” 

He nodded. “Best game I’ve seen in years. I’d forgotten how much of a sarcastic asshole Benny was. It was great.” He plopped down next to her still grinning.

“Did we win?” She asked. “Hell yes we won.” He replied. She smiled wider. “Good. Let me know next time, I want to go to a game. It’s been like two years.” He nodded. “Yeah, I want to go to a couple more this summer for sure.” He turned to look at the TV, quickly losing himself in the show she had on. For one night he wanted to not think about his miserable luck in love and just concentrate on the good day he’d had and how fun it had been. Now if everyone would just stop mentioning Cas, his life would be perfect. He had wanted to attend this reunion on the off chance that Cas might show, but now? The more he thought about it the more he knew that finding out that Cas was married with a family of his own would be too much to handle. In the morning he would call Charlie and break the news; he was going to pass on the reunion after all.

“Like hell you are Winchester!” Charlie snapped and Dean could feel her anger even through the phone lines. He sighed deeply. “Charlie…”

“Don’t you sigh my name you asshole! I know why you’re wanting to back out. You’re worried that Cas will actually show, and that he’ll be super hot with some model perfect wife and two point five kids and mansion in the Hamptons. I may not have seen you in twenty years Dean, but I know how you think, and you’re being ridiculous. You are coming to this reunion! I put my blood, sweat and tears into it planning this, and so did Lisa. I want people there that I actually like, and that means you, so stop your pity party and don’t make me drive up to Chicago and drag you down here.”

Dean was irritated, he couldn’t help it. Charlie had always known him better than anyone and had never been afraid to call him out on his bullshit. If she’d been straight and he’d been interested at all, he’d have probably married her a long time ago. She was the only person he let talk to him like that, and he could handle her bossy nature easily. “I can’t handle it though if he is. It took more than ten years to get over him, and since learning about this reunion he’s all I can freaking think about. I’m driving myself nuts over this, and for what? He never felt the same way about me. I’ve spent enough time feeling sorry for myself and longing for something I’ll never have. I just can’t do it!” 

“Dean, he asked about you. That’s something, right? What if he comes to this thing and you don’t show up? I know he’s sorry for what he said at graduation, and he wants a chance to talk to you. Don’t deny him that.” Her tone was softer, and it was when she pleaded like this that he found it the hardest to resist her. “Fine, I’ll go, but I’m not staying long.” He grumbled. “You’ll be glad you did. There are a lot of people coming that miss you.” She said. “Yeah, sure, whatever.” He hated not being able to stand up to her.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	10. Harboring Secrets

**Summary for the Chapter:**

> Cas thinks Dean just broke up with a girl and he tries to pressure Dean into admitting it. It causes a small fight between them.

September 1993

“What exactly are you doing?” Dean asked when Cas showed up at his house with a skateboard under his arm. “What do you mean?” Cas asked. This was the newest phase Cas was going through, wearing loose, baggy clothes, hair long and in his face, and getting around via a well-used skateboard. Dean was actually amused by it. 

He motioned toward the new earring Cas was sporting. “I mean what the hell are you doing wearing that?” 

Cas was grinning as he touched the stud in his ear. “I pierced my own ear last night. Didn’t hurt half as bad as I thought it was going to.” Dean gave an amused huff and shook his head. “You pierced the wrong ear.” 

The smile on Cas’ face faded. “What do you mean?”

“I mean that’s the side you pierce if you’re gay.” Dean explained, but he was even more amused now. Instead of his typical look of confusion Cas merely looked annoyed. “I’ll pierce whatever ear I want Dean, it’s my body.

Dean held up his hands in surrender. “I’m just saying. Personally I think it looks good on you.” He dropped his hands and stuffed them in his pockets. Cas’ smile was back and Dean was glad. It was his most favorite thing in the world. 

“Come on, let’s get to school. We’re upperclassmen now. No more getting pushed around. Dean said as he jogged down his front steps and went to his dad’s Impala.

“Whoa, you’re taking the Impala?” Cas asked, shocked. 

“He gave it to me the day I got my license. He’s using the truck now and Baby was just collecting dust in the garage.” Dean told him. Cas’ grin grew so wide Dean was able to see nearly every tooth in his mouth. 

“Sweet! Do you have to drive Sam to school?” 

“Not til next year. My mom still takes him while he’s in middle school.” Dean explained as he got behind the wheel of the car. Cas slipped into the passenger seat and laid his board across his lap.

“I always wanted to ride in this car.” He said as he ran a hand over the dashboard.

“Now you can every day.” Dean said with a silly grin of his own. Cas smiled back. “Yeah.”

It was a short ride to school but it sure beat the fifteen minute walk they would have had to make without the car, and when they got out Cas dropped his board and skated right up to the doors before picking it up again. He waited for Dean. With Cas’ new clothing style they couldn’t have looked less like friends if they had tried. Dean hadn’t changed at all, not in three years. He still wore his hair short, still wore jeans and boots with his dad’s old leather jacket, usually worn over a tee shirt or flannel. In winter it was often worn over both. Cas though seemed to still be trying to figure himself out. Freshman year he had been content to wear his polo shirts and baggy sweaters under a trench coat that was much too big for him. Sophmore year he’d had a brief Goth phase that had actually worried Dean while it was happening. This year, he was a skater. Dean knew what kind of crowd the skaters were, and he didn’t approve. All he could do was hope that Cas outgrew this particular one quickly. He really wanted Cas to cut his hair back into the messy style that it looked so good in. 

When they walked into school girls immediately flocked to Cas’ side. Dean couldn’t handle that so he silently slipped away to locate his locker for this year and pick up his books. Fifteen minutes later he was loading the books into his locker when a hand slammed against the locker next to his face.

“What the hell dude? Why’d you just disappear like that?” Cas asked, clearly annoyed. Dean kept his eyes on the books he was organizing rather than look up at Cas. He just shrugged. “You were…busy.”

Cas made a noise that sounded like he was disgusted. “Oh whatever. I’m not interested in those girls.” Dean took out his biology book and closed his locker. “Where’s your locker?” He asked. Cas shrugged. “I have no idea.” Dean rolled his eyes and opened his own back up. He grabbed the skateboard from Cas and shoved it inside. Cas made no complaint, he just followed Dean down the hall. 

“What is your first class Cas?” Dean asked. Cas pulled his schedule from his pocket. “Gym. What the fuck? Who has gym first thing in the morning?” 

Dean laughed and poked him in the chest. “Apparently you do.” Cas rolled his eyes and when they reached the second staircase in A hall they parted ways. “I’ll see you later.” Dean called out. Cas waved and continued on to gym. 

They didn’t have lunch together this year and Dean was actually pretty glad for that with all the rumors he’d been hearing about Cas’ exploits. He had a different girl practically every day. So dressing in baggy, mismatched clothing and wearing his hair long and stringy still drew the girls in. Dean tried to ignore the rumors, tried not to let it crush his heart and shred it into tiny, little pieces. By Dean’s count Cas had to have made out with close to two hundred girls, and that wasn’t just the one they went to school with either. The older he got, the better looking he got, and now he ever drew the attention of university girls. It sickened Dean. He dated a little, even had a thing on and off most of sophomore year with Tess, but he never slept with her. Cas avoided him though he had noticed, whenever he had realized Dean was dating her again. It was hard trying to find girls that hadn’t had their tongue down Cas’ throat, and that was a big reason why Dean kept going back to Tess, she wasn’t interested in Cas. The thought of kissing a girl that had made out with the boy he was so crazy about was too much to bear, so when he did initiate contact with a girl he was quick to make sure she hadn’t had been one of Cas’ discarded ones. It was like trying to find a needle in a haystack. When things no longer worked with Tess he dated a few other girls before deciding to check out girls at other schools. Instead, he found Rob. It was most of junior year that they dated, though they kept their relationship quiet. Neither thought their families would understand, and Dean wasn’t ready to announce to the world that he was bi. Of course Cas was nosey. He suspected that Dean was seeing someone though he knew it wasn’t a girl at their school. He needled Dean and bugged him as he tried to get it out of him, but Dean wouldn’t budge. He knew he was hurting his friend by not telling him, especially since they shared practically everything, but he didn’t want to lose Cas as a friend. Losing Cas would have killed him. When Rob, who was a year older announced that he was joining the Army it got Dean thinking. They broke up right before Rob left, and it was amicable for them both, and once Rob was gone Cas immediately noticed a difference in his friend.

“You and your girl broke up, right?” He asked out of the blue one afternoon while they were sitting on Cas’ couch watching cartoons. Dean frowned and sighed. Here they were going again.

“I have told you a million times, I didn’t have a girl.” 

Cas, now out of his skating phase and back into some semblance of normalcy turned to pin him with those blue eyes that Dean loved so much, except when they were staring at him like he was under a microscope as they were right now. “Dean.” Just his name, that was all he said, but it was enough to tell Dean that he still didn’t believe him. Dean was irritated now. He couldn’t help his temper and in moments like this it tended to flare up. He turned in his seat to glare at his friend.

“There was no girl, so drop it!”

Cas recoiled slightly at his outburst but he quickly nodded. “Ok, there was no girl. Sorry.” He turned back to the TV but Dean could see how his jaw was clenched and his hands were fisted in his lap. Immediately he felt guilty.

“I’m sorry I snapped Cas, but really there was no girl. I’m not lying.”

Cas turned to look at him again, his blue eyes dark and guarded. “There’s been something going on with you Dean, and it feels like you’re hiding things from me. And you don’t tell me who you’re dating, like ever. Why is that? Are you afraid I’ll make a move on them or something? Cause I wouldn’t do that to you.” Now he just sounded downright pouty.

“No, that’s not it Cas. It’s…complicated. I just have some things going on in my life that I’m not ready to talk about. With anyone. It’s not you. And trust me, I know you wouldn’t steal anyone I dated.” He had to fight against the smirk that wanted to twist across his mouth. No, no way Cas would be stealing Rob or any other guys he dated. Cas was still watching him as though he were suddenly a mystery that he was trying to work out. “But you’ll tell me when you’re ready?” He finally asked.

Dean nodded. “When I’m ready I will.” That seemed to be good enough for Cas, and Dean was relieved. They returned to watching cartoons, talking about whatever came to mind, and for a while things returned to normal for them.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	11. Reunion Time

June 2015

Dean was a nervous wreck. He went through his closet a dozen times trying to find something to wear that fit Charlie’s classification of semi-formal. Why had she chosen to host this in a banquet hall? Lexi didn’t seem to be having any problems finding clothes. She had a dozen or more dresses and she selected three to bring with her. She hadn’t yet made her mind up yet as to which one she wanted to wear. He was still standing in front of his closet feeling incredibly frustrated when he heard a knock at his bedroom door. It was already open but Lexi was being polite. He turned to look at her and noticed she was holding up a suit on a hanger.

“What’s that?” He asked. “I consulted mom and told her where we were going and she made some color recommendations. So I went and bought you this. I know you’re worried you didn’t have something that you’d look good in, but dad, you’ll look hot in this, trust me. Cas isn’t going to know what hit him.” She held it out and he crossed the room to take it from her. 

“Lexi, suits are not cheap, how much was this?” He asked as he turned it around to take a look. It was a cream color, light weight, and when he checked he was surprised to see she had gotten his size right.

“Don’t worry about the cost. I have a job, remember? And all of my classes are paid up. I wanted to do something nice for you.” She turned to leave. “Try it on, I want to see you in it.”

She left, closing the door behind her and he quickly stripped out of his tee shirt and jeans. The pants fit perfectly, as though they had already been tailor made to his measurements, and the white shirt was crisp and bright under the jacket. He looked at his reflection in the mirror over his dresser and smiled. He did look good. He was glad that after is years in the military he had continued to stay in shape. Forty was sneaking up on him and he didn’t want to get thick around the middle like most men his age were starting to get. This cream actually flattered his skin tone and the cut was great. Now he’d have a new suit for work too, if he dared to wear cream in a school full of obnoxious teenagers. He would have to give Trish a call late and thank her for helping Lexi pick this, but right now he wanted to thank his daughter.

Dean opened the door and went down the hall to the living room. Lexi was on the couch but she turned around when he walked in. She smiled and jumped up to hurry over and see him up close. “Oh my God dad! You look fantastic! Cas isn’t going to be the only one staring, everyone will be!” She gushed. He couldn’t help but smile. “You think so?” She nodded. “Oh definitely. I hear from all my friends about how hot my dad is. It freaked me out at first, but now I’m used to it. So I know if my friends are looking, so will everyone else. You’re really going to wow them.” He leaned down and kissed her forehead. “Thank you for getting this. I would have ended up wearing one of my suits for work, and those are all old.” She fixed his collar and straightened his jacket. “Now what kind of cologne are you going to wear? And how will you be styling your hair?”

Dean looked lost. “Cologne? My hair? What’s wrong with how I currently style it?” She gave him a look of pure exasperation. “Dad, you part it down the middle.” Like that was all she needed to say in order to make her point. She took him by the hand and dragged him back to his room where she started examining each of the bottles of cologne he had. She selected one, and he was grateful to see that it was actually his favorite, a gift from his mother a few years earlier that he hardly wore so he still had most of the bottle. She grabbed his comb and worked it through his hair, fixing where he usually parted it, and styling it closer to how he wore it when he was a teenager. When she was done she stood back to admire her work. “I hope you have shoes, I didn’t buy any.” She said. 

He looked down at his bare feet, wiggling his toes. “What, the beach bum look isn’t in?” She laughed and went to his closet. Luckily he had a rather comfortable pair of tan dress shoes that would work nicely with this suit and she grabbed them up. 

“Let’s get you packed.” 

While Dean took off the suit and packed it in the special garment bag so it wouldn’t wrinkle Lexi worked on packing his nicest jeans, a couple of dress shirts, and a couple of tee shirts. She added in his boxers against his protesting that he could pack those himself, but she argued that she already did the laundry and knew full well what his underwear looked like. Once she was sure he had enough to last him for the three days they’d be back in Lafayette she went to finish her own packing. They were leaving first thing in the morning. Dean was fairly certain he was not going to be able to sleep.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	12. First Time in Twenty Years

**Summary for the Chapter:**

> It's time for the reunion, and time to face up to his past.

Reunion

Dean had to force himself to breathe slowly as he pulled the Impala into a parking space near the middle of the parking lot. Lexi was sitting next to him and she reached over to pat his leg. “It’s ok dad, these are the same people you knew twenty years ago, just a little fatter, a little balder, and a little sadder. You are going to knock them dead. You still look like a model. Everyone’s going to be so jealous.” He gave her a tentative smile and nodded.

“Let’s just get this over with.” He sighed as he got out. She got out and when he came around to her side he offered her his arm and she smiled as she took it. They walked toward the building and he could see other people walking in as well. From this far away he didn’t recognize anyone, but it had been twenty years after all. 

Inside they followed the signs up to the second floor and found themselves entering a rather spacious banquet room complete with crystal chandeliers and a dance floor. To their left was a table with three ladies seated at it. Bright red hair immediately caught Dean’s attention. Charlie gasped when she spotted him. “Dean! Oh my God you’re gorgeous! Not that you weren’t always, but damn!” She was already on her feet and pulling him into a hug. He hugged her right back. 

“Thanks Charlie. You look great too.” He liked the tight black dress she was wearing. It hugged her curves and made her flaming red hair stand out even brighter. She motioned to one of the ladies at the table who stood up and came over. “Dean, I’d like you to meet my wife, Stacy.” The woman was attractive with long, dark brown hair and an hour glass figure. A bit of a change from the girls Charlie had dated back in school, and definitely an improvement. He shook her hand. “Nice to meet you Stacy. It’s nice to know someone can put up with Charlie’s bossy nature.” He winked at Charlie who scoffed and punched him in the arm. Stacy just laughed. “Well, it’s one of the things I love most about her. That and her fire red hair.” She looked over at Charlie with an affectionate smile, and Charlie just smiled back. 

“Come here, check in, and get your name tag.” Charlie pulled him over to the table and he signed in and accepted the name tag the woman in the middle was handing him. When he looked up he had to do a double take. 

“Lisa?” He gasped. She gave him a tight smile and nodded. “Hi Dean.” Apparently she still was holding a grudge over their Facebook chat a few months earlier. He reached back to take Lexi’s hand and pull her closer. “Lexi, do you remember me telling you I dated a girl named Lisa my senior year?” He asked. She nodded. He looked back at Lisa. “Well, this is Lisa. Lisa, meet my daughter, Lexi.” Lisa smiled up at the girl. “She’s your clone. She’s beautiful.” Lexi smiled back and offered her hand. “Nice to meet you Lisa. My dad said nothing but nice things about you.” Lexi told her. Lisa’s smile brightened as she turned to look back at Dean. “Well, I hope you both have a wonderful evening. Dinner will be served at eight.” Dean took a nametag for Lexi and filled it out before sticking it on her. Then he took her by the hand and led her further into the room. Right away he spotted Benny and Andrea. They talked for a bit before other people started wandering over to say hello. Tess even made her way over and Dean gave her a warm hug before introducing her to Lexi. The room was filling up quickly and he was impressed to see how many of his former classmates had actually come. He couldn’t help but keep glancing back towards the door and Lexi noticed. She gave his arm a squeeze and watched the door with him. She didn’t know what Cas looked like but with her dad’s description she figured he would stand out from the rest. After a half hour of socializing Lexi excused herself to go and get a soda at the bar. She was waiting for the bartender to finish refreshing drinks for a lady at the other end of the bar when she felt someone step up next to her.

“Well, I certainly don’t remember you in my graduating class. You look a bit….young.” A deep, gravely voice was saying. Lexi turned to face the man talking and found herself looking at a guy so gorgeous it took her breath away. He had bright blue eyes full of amusement, and a soft smile on his face. His eyes flicked down to the nametag on her dress and the smile dropped away immediately. When his eyes next met hers they were filled with a mixture of surprise and fear.

“You’re here with Dean?” He asked. He wasn’t wearing a nametag but from the dark hair and blue eyes she knew she was standing here with Cas.

“Yes I am, and you’re Cas, right?” She somehow managed to say. He nodded, his eyes scanning the crowd, but even she couldn’t see her dad from here, not with Benny blocking him.

“I hadn’t realized Dean was married.” He sounded…disappointed. Immediately she reached out to place a hand on his arm.

“Oh! I’m not Dean’s wife! I’m his daughter!” 

Cas turned back to look at her, a curious expression on his face. “He has…kids?” She nodded. “Yes. I’m Lexi, I’m nineteen, and my brother Connor is seventeen.” She could see the wheels turning as Cas did the math. Yep, her dad got his first girlfriend out of high school pregnant, and Lexi was the result. “My dad’s not married. He got divorced last year. My stepdad was cheating on him through most of their marriage.” She explained. Cas blinked. “Excuse me?”

Oh crap…that’s right…Cas didn’t know her dad was bi…

Her mouth opened but she couldn’t think of anything to say that could fix that, so she shut it again, biting down on her lower lip.

“Did you just say Dean was married to a man?” His eyes narrowed, but to her surprise he didn’t look upset by the news. He actually looked…pleased.

She nodded. “My dad is bi, but he likes guys more. He met my stepdad when I was about six. They dated for a few years and then got married. But like I said before, he was a cheat and my dad kicked him out.”

Cas’ eyes went wide and he turned to search the crowd again. She reached out to touch his arm and he looked back at her.

“He’s going to completely hate me for this, but you were his first crush. He was in love with you all through high school. He knows you’re straight, but-” 

This time it was Cas that raised a hand, placing it over the one she still had on his arm to silence her. “Honey, I’m not straight. I was in love with your dad since the first moment I laid eyes on him, but I thought he was straight! Oh….that explains a lot…” His eyes got a dreamy, far away look in them as old memories began to replay, and then he grimaced. “He never would have known though, I tried so hard to appear straight back then. I couldn’t tell him I wasn’t because my own family would have disowned me. Eventually they did, but that’s water under the bridge now.”

“Are you married? Involved with anyone?” She asked. He gave a sad smile and shook his head. “No, I was with someone for a while, but it didn’t work out. Plus I couldn’t get your stupid father out of my head. I really messed things up in the end.”

Lexi looked to see if her dad had noticed that she was still missing. He was engrossed in a conversation with Benny, so she had at least another few minutes. She turned back to Cas.

“He was afraid to come tonight, to face you. He thought you’d hate him, and he was terrified that you’d be married to some like, supermodel or something. The way he talks about you in high school…” She left that off, not wanting to repeat those particular stories. Again Cas grimaced. “I know, I was awful, but I was extremely confused. I didn’t know any gay people back then, with the exception of Charlie, and I didn’t understand my feelings, so I kept them bottled up, and I decided that I needed experience with girls so I would know whether I liked them or not.” 

“Over two hundred girls though? After the first three or four you couldn’t figure it out?” She asked dryly. He let out a soft laugh. “I was young and I was stupid and they distracted me from how I felt about your dad.”

“He said you guys got into a fight junior year because you thought he was dating some girl.” She said. He had to think for a moment, but then it came to him. He had been jealous thinking Dean had a girl he’d been dating most of the year. And then Dean had yelled at him and it had confused him because he had been so certain…

“It was a guy named Rob actually.” Lexi said, one eyebrow cocked as she waited for the information to sink in. Cas actually slapped himself in the forehead and groaned. “I was such an idiot!”

“The only thing he won’t really talk about is why you guys got into a fight at graduation. He clams up whenever I mention it, but I know it hurts him. I don’t think he’s ever really let himself truly be happy, not since whatever happened between you two.” 

Cas nodded. Of course. He had opened his mouth and using words alone he had torn Dean to pieces, and he had been too scared to go apologize to him later. As he thought about the last time he had seen Dean he began to explain.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	13. Cas' Confession

**Summary for the Chapter:**

> Cas tells Lexi exactly what he said that caused the rift between him and Dean.

June 1995

They were standing in the middle of the football field, new graduates ready to start their lives beyond high school, and all Cas could think of was how stupid Dean was for enlisting in the Army. He had gone and done it without ever saying a word to anyone, and since he was already eighteen he didn’t need to consult his parents either. He was just now telling Cas about it, and Cas was furious. He couldn’t quite figure out why though, other than that he had an irrational fear of being separated from Dean, and so he lashed out at him.

“You used to tell me everything Dean, but not anymore. You keep secrets about the girls you date, you sneak around doing God knows what, and you join the Army? The freaking ARMY?! And you don’t tell me anything! What am I supposed to say here Dean? You want me to be happy for you? Because I’m not! This was a stupid, selfish decision you made and I do not support your decision to join the military!” He was practically screaming, too furious to register the look of hurt and betrayal on Dean’s face. Then Dean was getting angry too.

“Fine Cas, you don’t have to support me! It’s my life anyway, not yours! I’ll do what I want with it! If you can’t support me then I don’t see any reason why you’re still even standing here talking to me. Clearly you think I’m a bad friend and a stupid person!” Dean roared.

“Yes! You are very stupid Dean! People die in the Army! You might not come back!” That was what terrified Cas more than anything, that Dean might never come back.

Dean’s expression hardened and there was pure fury flashing in those green eyes of his. “Well I’m sorry you feel that way. Maybe if you had listened when I tried to talk to you instead of constantly shoving your tongue down some girl’s throat you might have been up to speed on what was going on in my life! There’s so much I wanted to share with you, but you are always so damn busy with your own drama that you never listened, and I wasn’t sure you could handle the crap I wanted to tell you, so I just kept it to myself. Seeing how you’re reacting now? I’m glad I didn’t say anything!”

“Fuck you Dean. I was always there for you. I always listened when you had something important to say.” Cas snapped.

“No, see, that’s your problem, you listen when it’s convenient for you. Did you know that last year Sammy almost died? Yeah, that cold he had? It was strep and he got a heart infection. But no, you were busy working your way through the university cheerleading squad! You are never there for me Cas! Never!”

“You want to see how never there I really am Dean? Drop dead. Don’t bother ever calling me or stopping by again. We’re done being friends.” And with that Cas had turned and walked away, regretting every word that had left his mouth, and forever regretting not telling Dean how much he truly loved him. His heart broke that day, and he was never able to put it back together.

**Notes for the Chapter:**

> All chapters will be posted today. If you like it leave a kudos and a comment.


	14. Apologies and Secrets revealed

**Summary for the Chapter:**

> Cas and Dean FINALLY tell each other how they feel, and Cas apologizes for everything.

Back to the Reunion

“Oh, Cas…my dad joined the military because my grandpa wasn’t making enough to cover my Uncle Sam’s medical bills. The insurance wasn’t enough and my grandpa was struggling bad. My dad signed up and sent every check home, and it helped cushion the expenses. My uncle eventually needed a heart transplant. He’s doing well now. He’s married and just had a baby. He’s a lawyer, just like my dad always knew he would be.” She offered him a sympathetic smile and he smiled back.

“You know, I can see it now. You look a lot like your dad.” He studied the girl’s face. She could almost be Dean’s twin, she looked so much like him. Her hair was lighter, actually a honey blonde, and she had his bright green eyes and freckles too. She was a lovely girl.

“Yeah, I get that. You know, if you thought he was hot back then, you should really see him now. He’s gorgeous.” She said, nudging him gently.

“I’m sure he still hates me. Hell, I hate me for what I said that day.” He looked over to where Dean was standing, and realized that Dean was looking right at him, eyes wide with shock.

“Oh shit.” He muttered. Lexi looked over and saw her dad looking at them. There was fear in his eyes and she could only imagine what was going through his head. She motioned for him to come over and for a moment she was sure he wasn’t going to budge, but then he slowly started toward them.

“My dad doesn’t hate you, he’s in love with you still.” She said quickly before her dad was within earshot, ignoring the look of surprise on the dark haired man’s face. When Dean reached them he stood stiffly next to his daughter, his eyes looking past Cas toward the door.

“Uh, hi. I see you met my daughter.” His voice was strained and he grimaced at the sound of it. Cas lifted his head to look at Lexi and then over at him.

“Yes, she’s a lovely young lady. We were just talking about…stuff.” Wow he felt stupid and awkward suddenly. 

Dean eyed his daughter. He knew what she was capable of, and how she liked to pry where she had no business. Plus he had no idea how long they’d been standing here talking, or how she had even figured out this was Cas since he wasn’t wearing a name tag. 

“Cas here is a very nice man dad. We had a lovely conversation, but if you’ll excuse me I have to visit the ladies room.” She slipped between them and hurried out the door, leaving them standing there in awkward silence. Cas decided to break it first.

“So I heard you’re divorced?” The look on Dean’s face made him think that maybe that wasn’t the right topic to start off with.

“Uh, yeah. Been a year in February.”

“I’m sorry it didn’t work out.” Cas said, and he meant that. The only thing he had ever wanted was for Dean to be happy.

“Yeah, well, it happens when people can’t stay faithful.” Dean muttered.

“Yes, your daughter was telling me about that. I’m so sorry that happened to you.” 

Dean turned his gaze on Cas finally, and he could see the intensity in those green eyes.

“What exactly did she tell you?” There was a demanding tone to Dean’s voice and Cas immediately regretted that this was the first topic he had chosen to bring up. Rather than rat Lexi out completely he opted to give a vague answer.

“She said you were married for a few years but it didn’t work out.”

“Uh huh. And she didn’t tell you I was married to a man?” Dean asked. The lack of shock on Cas’ face confirmed it and he nodded. 

There was no lying now, not even to spare the poor girl. He nodded. “Yes, she did mention that. And that’s ok, if you thought I was going to have a problem with it, I would never.”

Dean’s expression darkened. He was guarded, Cas could tell. Even after all these years he still remembered Dean’s defense mechanisms. He decided it was time to just come clean and tell Dean everything.

“Can we go sit down and talk? There are some things I need to tell you, and I think perhaps we might find a bit of privacy over there.” Cas nodded toward the empty tables at the other end of the room. For a moment he wasn’t sure Dean would agree, but finally he nodded. 

Cas led the way to the table furthest away and motioned for Dean to have a seat. Once he sat down Cas sat right next to him. He took a moment to really look at Dean. He had been gorgeous back in high school but now? There wasn’t an accurate word to describe him now. He had filled out, and the suit he was wearing made him even more attractive, if that was even possible. There were even more freckles spilling across his nose and cheeks, and they just added to his overall beauty. Dean Winchester was still the most gorgeous man he had ever laid eyes on, even though he was sitting here looking extremely uncomfortable. He blamed himself for that. Dean was sitting very stiff and he had his hands balled up on his thighs, but at least he was looking in Cas’ direction. He took that as a good sign.

“Ok, before I can fully apologize for acting like a complete and total ass after graduation, I need to explain a few things so you understand why I was such a moron.”

Dean frowned. “What are you talking about exactly?” 

Cas took a deep breath and leaned closer. “Dean, I’m gay.” He paused as the words began to register. Dean’s eyes went wide and for a moment his jaw was working, trying to find something to say, and failing. Cas held up a hand to stop him.

“I can only imagine what is going through your head right now. So let me start by saying that all through high school I was absolutely positive you were straight, and I was determined to be straight too. You knew how my dad was. He would have disowned me and kicked me out of the house, even as a young kid. You don’t understand how cruel that man can truly be. I only learned the true extent after I came out to him. That was a nightmare in itself and I’d rather not hash that part out right now.” He looked up at Dean who nodded.

“I remember how your dad was.” 

“Right. So, that being said, I was kind of sort of in love with you, but like I said, I thought you were straight. You never alluded to anything else, and no one hinted that you weren’t, so I just went off what my stupid teenage brain was telling me at the time. I didn’t know any gay or bi people at the time, with the exception of Charlie, but I had a hard time basing anything off her behavior, and she never talked to me about you. She was always a better friend to you than she was to me, so she never said a word, if she even knew at all.” 

Dean let out a small laugh that sounded bitter. “She knew.”

Suddenly Dean shifted in his seat so that he was facing Cas, his eyes intent and demanding. “So what the hell was up with all the girls?”

Cas couldn’t help the look of absolute embarrassment. “It was my brother’s suggestion. I think he suspected I was gay before I even knew I was, and he said that if I wanted to fit in and if I wanted to find a girl that I could be with, then I needed to test the waters. His words, not mine. I tested the hell out of the waters to no avail, because I only ever wanted you. Took a lot of kissing in my attempt to stop liking you but it didn’t work. You filled my every thought, even when I was with a girl. I drove myself half mad just trying to stop thinking about you.”

When he looked up at Dean again there was shock on the man’s face. “So let me get this straight. You kissed more than two hundred girls in an attempt to stop thinking about me?” Dean raised on eyebrow. Even Cas knew how it sounded, but it was the truth.

“I thought about you a lot.” Cas replied sheepishly. And finally there was a break is Dean’s defenses. His mouth began to turn up in the corners and he shook his head.

“Dude, I had the biggest crush on you all through high school but I thought you were the straight one! And I have to admit, it hurt seeing you with all of those girls. I started dating girls at other schools because I couldn’t stand the thought of kissing one that you had already kissed. Not when I wanted to be the one kissing you. I envied every single one of those girls.” There was a blush rising on Dean’s cheeks and he wanted to kick himself for it.

“Now at least I can properly apologize for the last words we shared. See, I was jealous of the girls you did date, and I only recently learned that you dated a guy too. If I’d have known that back then, trust me, I’d have come clean in a heartbeat, but I had no idea. I just knew I was envious of anyone that got to kiss you or hold you, and it felt like you were keeping secrets from me. Looking back I guess we both were, but I was crazy with jealously, and I was terrified of you leaving me, and in the end I was the one that ended up pushing you away. I shouldn’t have done that, it was the fear talking. I was too scared to call you. I thought that you hated me, and by the time I did work up the nerve about a week later, you had already left for basic. I heard that through Benny. I just want you to know that I’m so sorry, I was selfish and stupid and scared. I don’t expect that you’ll forgive me, but I needed to tell you how truly sorry I was.” Cas could feel the burning in his eyes and he wiped away the tears before they could actually spill. He was startled when a warm hand closed over the one he still had resting on his thigh.

“Cas, I forgave you a long time ago. I knew it was anger and fear talking, I just didn’t understand why, and you didn’t let me explain why I was joining, though I’m sure Lexi has filled you in on that. You know, I never stopped missing you. I’ve always cared about you.”

God how he had missed Dean’s smile! It was the most beautiful thing in the world. “What have you been doing all these years Dean? Besides serving in the military and having kids.” Cas asked.

“Well, I did six years in reserves, paid for my brother’s medical expenses as much as I could. I met a girl named Trish right after basic and she was the first, and last girl I slept with. First time and whoops! We ended up with Lexi. I tried to stick it out and two years later we had my son Connor, but she was mad because I wouldn’t marry her, so she took the kids and left. I got joint custody and we’re friends now. She understands. Anyway, I met my ex-husband while I was studying to become a teacher. He was in a couple of my classes. We hit it off, dated for a few years after my stint in the Army was over, and then we got married. Huge mistake. He turned out to be a liar and a cheat, and two years ago I kicked him out. Last year in February the divorce was finalized. I did complete my degree and I now teach AP English Lit. That basically sums up the last twenty years for me. What about you?” Dean asked.

“Well, my life has been pretty dull actually. I moved out after high school, went to college and earned my degrees, bought a house, and I met a great guy named Mike. Well, I thought he was great at first. Turns out he was controlling and meaner than a rattle snake, so after four miserable years I broke up with him. I’ve been alone ever since. That was about nine years ago.”

“What do you do for a living? And where do you live?” Dean asked.

“Oh, Chicago. I teach as well, at a magnet school.”

Dean’s jaw dropped. “You have to be kidding me, you’ve been in Chicago this whole time? I live in Chicago!”

“Seriously?” Cas asked. Dean nodded. “I’m over on Central and Grace, where are you?”

“Grand and Harlem!” Cas replied excitedly. All this time he had been so close to Dean. He could have apologized years ago!

Dean still had his hand over Cas’ and Cas turned his hand over so their fingers would intertwine. “You have no idea how much I’ve missed you.” He said.

Dean gave a small laugh. “Actually, I have a pretty good idea.”

Lexi stood near the door watching her dad talking with Cas. She watched as the tension left his body and he reached over to place a hand over Cas’. It warmed her heart to see them smiling at one another, and to see the love that was still in both of their eyes. When a hand came to rest softly on her shoulder she turned to see Benny and his wife standing there. He too was watching her dad with Cas.

“That should have happened twenty years ago. We all thought they belonged together. Apparently they were too stupid to see it though.” He said.

She looked back at her father and smiled. “Well they see it now.”

Dean spent the rest of the reunion sitting at that table holding hands with Cas, whispering and talking, touching every chance they got. Lexi stopped by the table long enough to eat and then excused herself. She later texted her dad to tell him she was going to go stay with Aunt Ellen and Uncle Bobby, and that he could enjoy their hotel room all to himself. As he read the text he couldn’t help but blush.

“What happened?” Cas asked. Dean slipped the phone back in his pocket. “My daughter decided to go stay with Bobby and Ellen. She’s leaving me alone in the hotel room tonight.” He rubbed nervously at the back of his neck. When he dared to look up at Cas he could see amusement in those blue eyes. “Oh, I see. What hotel are you staying at?”

“The Hilton Garden Inn right down the street.” Dean replied. Cas smiled. “Oh, that’s a nice hotel.” Dean shrugged. “I don’t get to travel much so I splurged. I wanted something nicer than a Motel 6.” 

“Oh, I get it. I was just going to drive home tonight. I didn’t anticipate staying this long. It’s getting pretty late.” Cas checked his watch though he was fully aware of the time. He was looking up at Dean hoping beyond hope that he would invite him back to his room tonight, though he was sure that was going to be pushing things. Dean really seemed to be considering it too. When Dean finally smiled Cas knew he was going to asked.

“It is getting pretty late, and like, I have a second empty bed now, you could, you know, stay with me if you want. Save yourself a two and a half hour drive back in the dark since I already paid for my room.” Dean’s face was burning so bad that even the tips of his ears were on fire, but when Cas smiled it was totally worth it.

“If you’re sure it’s alright.”

Dean nodded. “Absolutely.”

“I’m getting kind of tired now actually.” Cas said knowing full well he sounding nowhere as casual as he was attempting to sound.

Dean cocked one eyebrow and smiled. “Already? Yeah, I guess it is a long drive down here. I’m pretty tired myself. What do you say we get out of here?”

Cas smiled and nodded. “That sounds like a plan.”

They stood up, hands still locked together, ignoring the few surprised looks they were getting as well as the look of disdain from Lisa and started for the door. Benny nodded in Dean’s direction, a smug smile on his face, and Dean just smiled and nodded back. Charlie stopped them before they could leave though. She looked down at their hands and smiled. 

“You know, we all knew you two had the hots for each other back then.” She said.

“And you didn’t think to let us in on that?” Cas asked.

Charlie shrugged. “Honestly? We thought you guys would have figured it out on your own. Not our fault you two are romantically stunted.”

“Not anymore. We know exactly where we stand now.” Dean said, looking over at Cas. There was so much love in the other man’s eyes that it made his heart swell.

“Good. Now don’t be strangers. I hope you guys enjoyed tonight.” She gave them both a hug and a kiss.

“It was better than I could have ever hoped for.” Cas told her, and Dean smiled at that. “Same here.”

They said their goodbyes and made their way downstairs. People they both knew were lingering around and they said their goodbyes to everyone before starting across the parking lot. Cas laughed and clapped his hands in delight when they reached the Impala.

“I can’t believe you still have it!” He exclaimed. Dean’s face shown with pride.

“I could never get rid of Baby.” 

“I’m glad you didn’t. She’s magnificent.” 

“So where are you parked?” Dean asked. Cas pointed further down the parking lot. “I’m down there. I have a Scion.” 

“Follow me then.” Dean said, and got behind the wheel of the Impala. He pulled out and followed Cas up to an obnoxious candy apple green Scion that was parked near the lot entrance. Somehow it didn’t surprised him that Cas would be driving something like this. It suited him.

**Notes for the Chapter:**

> Almost done...
> 
> If you like it leave a kudos and a comment.


	15. Hotel Room Confessions

**Summary for the Chapter:**

> Confessions continue once they get back to the hotel room.

The hotel was right down the street and Dean pulled into the first parking spot he saw. Cas pulled in two spots over and was out of his car before Dean was. As they walked inside Dean took his hand and they headed for the elevator.

“You already checked in?” Cas asked as they rode up to the third floor. 

“Lexi and I got here this afternoon and we relaxed for a couple of hours before we went to the reunion. Sorry if the room is a mess, Lex may have left clothes laying around.”

Dean stopped in front of room 327 and opened the door. He stepped aside to let Cas in and then it dawned on him that Cas didn’t have any bags with him.

“Oh, you don’t have anything to sleep in.” He felt stupid saying it and decided to change the subject. “So…you thought I wouldn’t talk to you?”

Cas sat down on the far bed looking rather miserable. “I didn’t know what I was thinking. I came with the explicit intention of apologizing. I was hoping we could at least be friends again.”

Dean chuckled and laid his jacket over the back of the desk chair in the corner. “I have news for you Cas, the only reason I came tonight was for you. I’d have talked to you no matter what, though I don’t know what end it would have come to without Lexi opening her mouth.”

“I’m glad you brought her.” Cas said, grinning. “Me too.” Dean laughed. He was going to have to thank his daughter later for looking out for him.

Dean went to the closet and fished a tee shirt out of his bag and realized he hadn’t brought any pajama bottoms with him. He pulled out the other tee shirt he had brought with and offered it to Cas.

“I didn’t pack well, I usually just sleep in a tee shirt and boxers, and I didn’t think to pack more than a couple of tee shirts.” 

Cas accepted the shirt and began unbuttoning his jacket. He laid it on the other end of the bed and loosened his tie. Dean sat on his bed facing Cas and an awkward silence felt between them. 

“You know, we always used to have something to talk about.” Dean finally said. Cas smiled and nodded. “You’re right. So what do you do for fun?” He was trying to make small talk but it still felt uncomfortable. The sexual tension in the room was stifling. He just wanted to climb on top of Dean and pin him to the bed as he explored every inch of his body. Sitting here making small talk was just weird, and Dean must have felt it too because the look on his face shifted to one of confusion.

“Uh, well, I still play guitar.”

Cas’ smiled and Dean was instantly reminded of the way it used to make his heart beat faster.

“Really?” 

Dean nodded. “I still have the guitar too. Never bought a new one.” Cas understood the meaning behind what Dean was saying and it touched him in a way he hadn’t thought he’d ever experience with this man again. It had brought him incredible joy to buy the guitar in the first place from his brother and give it to Dean, but knowing that after all these years, and after the fight they’d had, he had kept it? That spoke volumes to Cas about how Dean felt about him. He stood up and moved over to sit next to Dean. Dean shifted a little to face him and Cas took his hand again.

“Dean, I know I’ve already said it, but I’m sorry for what I put you through back then. I was such an asshole. But I want to make it up to you now. I was in love with you when we were kids. Like actual love, and even though I was struggling with my sexuality, that was the one constant that I was sure of, and even after the fight I-” Cas took a deep breath and met Dean’s gaze. “I never stopped loving you. A part of me always has. I wondered where you were, what you were doing, if you were happy. I worried about you. But I had no idea how to find you. I spent years looking for you on sites like MySpace and Facebook, but you were never on them. I wanted to apologize for so long.” He closed his eyes as his voice broke, the sorrow and misery he’d been fighting for two decades now overwhelming him. He didn’t feel worthy of Dean’s forgiveness. Dean’s hand against the side of his face, thumb softly stroking his cheek was what made him open his eyes.

“Cas, I was in love with you too. It wasn’t just a crush back then, and yeah, the stuff you did, it hurt. A lot, but I get it now, and I’m ok with it. You don’t have to keep apologizing. It’s already accepted, and I know you’re not going to hurt me again.”

Cas shook his head. “I promise I won’t ever hurt you again!”

Dean smiled. “I know, and I want you to know that I’ve spent the last twenty years thinking about you too. I told my kids all of the crazy stuff we did, and all the places we went, and yeah, I told them how crazy I was about you. I don’t keep secrets from them. I learned a long time ago that secrets destroy relationships. Lexi and Charlie convinced me not to back out today. They told me that I needed to talk with you, to make amends, and to tell you how I felt, even if you had never reciprocated it. I can’t tell you thrilled I am that you’re gay. Like, you have no idea. And I never stopped loving you either. You were always in my heart Cas, and you always will be.”

Cas shuddered as the tears he’d been fighting began to spill and Dean pulled him against him, wrapping him tightly in his arms. Cas clung to him, afraid that if he ever let go he would lose this man again, possibly forever this time.

“Shh, don’t cry.” Dean spoke softly, his words soothing as his fingers combed through the mess of hair on Cas’ head. When his tears had finally subsided Cas turned his head so that his cheek was resting against Dean’s shoulder. 

“For twenty four years, since the first moment I saw you in A Hall I wanted to kiss you, do you know that?” He asked, his voice small and distant as he remembered their first meeting, of coming upon the tall blonde boy standing in the middle of the hall, and how when the boy had turned to look at him he swore he was looking upon heaven itself. 

“Then what are you waiting for? Another twenty four years to pass?” Dean asked. Cas pulled back to look up at him, those blue eyes that he loved so much wide and full of hope. Before Dean could say something else Cas leaned in, kissing him softly, and Dean sighed. He had waited so long for this, and it was everything he had ever hoped for. Cas’ fingers found their way up to his neck where they scratched gently at the short hairs on the back of his head, eliciting a soft moan from him. Dean pulled Cas closer, opening his mouth to meet Cas’ tongue as it slid across his lower lip. Kissing Cas was exactly as he had always hoped it would be, gentle and loving, and perfect. 

When they finally sat back Dean couldn’t help but stare. Cas had been absolutely beautiful twenty years ago, but now? He was absolutely breathtaking. The boyish features gone now, replaced by strong cheekbones, full lips, thick, dark lashes that made him look as though he belonged on a runway rather than a classroom. And he had grown a few more inches too! He was only about three inches shorter than Dean was. Back in high school Dean had towered over him for nearly all four years. And he was no longer the scrawny boy he’d been. No, Cas’ body was lean and even in a suit Dean could tell his body was toned and firm. And then he was smiling up at Dean again.

“We were both idiots back then, weren’t we?” It wasn’t so much a question as it was a statement when Cas spoke it, but Dean was smiling and nodding. “Yeah, we really were.”

“I wish I could go back to the first day I met you so I could have told you how I felt. I just feel like we wasted so much time.” Cas sighed, his smile now tinged with sadness. Dean brought a hand up to gently caress his cheek. Those blue eyes he had spent so many years trying to forget to no avail were now looking up at him, and the depth of the emotion in them was almost more than Dean could bear.

“I love you Cas. I always have, God help me.” He said softly. Cas blinked, his eyes wet again, though tears were not yet spilling. He smiled and Dean could feel the years of pain and loneliness at not having Cas in his life slipping away. “I love you too Dean, and I always will.”

“Did you go to the ten year reunion?” Dean asked suddenly, catching Cas off guard.

“Actually, I did, but I lost touch with most of the people I saw there. I only went because I was hoping you would come. I left after an hour when I realized you weren’t showing.”

“I didn’t go because I was with Scott. I wanted to, but I didn’t want to bring him and he’d have insisted on coming. We were engaged at that time.” Dean said as he dropped his hand from Cas’ cheek and felt the shame that washed over him. He’d been afraid Cas would be there, and he didn’t want him to see him with Scott, so he’d not even mentioned the reunion to him. Cas reached out, putting his hand on Dean’s thigh.

“I get it.” He said softly. And really, he did. “I was with Mike at the time, but we were on the rocks and I left him at home. I wouldn’t have brought him anyway, he was an ass around my friends. None of the people I wanted to see came anyway. I was mostly there for you though.”

Dean shook his head. If he had just gone he could have made amends with Cas ten years ago. “I wish I’d gone.”

Cas moved his hand a little higher and squeezed gently. “But you’re here now.” He leaned in, capturing Dean’s mouth again, and with his free hand he grabbed the back of Dean’s neck and pulled him in closer. He was still in awe over the fact that he was sitting here kissing Dean. Dean! The only person he ever wanted to kiss again. This time he was the one to pull back. There were still things he needed to say.

“Dean.” He said and waited for those beautiful green eyes to open and look at him. “Yeah?”

“I wanted to tell you that the way I behaved in high school, I’m not like that anymore. After I said those horrible things to you I went home and I seriously contemplated killing myself. I was gay in a family full of religious nuts, and I had just lost my best friend, who I was in love with. I cried for a week. It was my brother that came and talked to me. Turned out he already knew, and he is the only person in my entire family that accepted me as I am. He’s the only person I still talk to. Anyway, I confessed my feelings for you, but apparently he knew that already too. He’s the one that told me to go talk to you, but when I did, you were already gone. I went home and I seriously contemplated my life. All the mistakes I’d made, all the pain I’d caused you, and I was sitting in my room with a bottle of pills I’d snagged from my mom when Gabe found me. He took them away and then he sat with me all night. He assured me that one day I’d find you and I’d get the chance to tell you how I felt, and that I was sorry. And then he stood by my side two days later when I came out to my parents. That was a disaster of course and they kicked me out on the spot. I’d actually already packed in anticipation of it. The minister at our church actually took me in briefly and helped me get an apartment. Gabe moved in with me a couple of weeks later. Turns out he’s bi. Apparently I gave him the courage to come out as well, and our parents kicked him out too. I got a job and I started college, and I focused on my degree, but I never stopped thinking of you and looking for you. I never so much as even looked at another girl after I came out, and I hardly even looked at guys either. They weren’t you. Mike? I don’t even know how that happened really. I think in the beginning he somehow reminded me of you, but then he showed his true colors, and I realized he was everything I hated. I preferred to be alone than to be with anyone. I fully expected to spend the rest of my life alone. This was kind of my last ditch effort to apologize to you and all I had hoped was that you would at least consider being my friend again. My life isn’t the same without you in it.”

Dean smiled and leaned in, kissing the corner of his mouth gently. “That was very Hallmark moment of you Cas. They could make a movie off of our drama.”

Cas rolled his eyes but couldn’t help but smile. Dean was right.

“Well, it’s good to know you weren’t playing the field all these years. That was actually kind of my worst nightmare. I worried about all the crap you could have been out there subjecting yourself to. I didn’t play around either. I met Trish on accident, she was the older sister of one of Sam’s friends, and she was pretty and she liked me. I was messed up for a long, long time after the fight you and I had and Trish, she just wanted to make me forget how much I was hurting. I hadn’t told her exactly why I was so hurt. She thought a girl had broken my heart. So I tried to let her. I thought I could be happy with her, but as much as I tried, I wasn’t. I figured that out around the time we learned she was pregnant with Lexi. I wasn’t even sure why I slept with her in the first place, but I wasn’t going to be one of those guys that walked out on their pregnant girlfriend, so I stuck it out. I actually stuck it out for four years. By the time Connor was one she was downright nagging me to propose, and I had to come clean to her. She was so mad at me. I was away for a training weekend and when I came home I learned that she had packed up half of our apartment and taken the kids. I had no idea where she even was, but Sam knew, and he told me. We fought for several years before we reached a point of agreeable peace. I got joint custody of my kids and I continued working on my degree. It was not long after we split that I met Scott. I wish to God I’d never agreed to go out with him, but hey, we all learn lessons the hard way, right? I dated him for almost seven years before he popped the question. I knew he had cheated on me more than once, but I thought he loved me. We got married and it was the most miserable next seven years of my life. I was happier with Trish than I ever was with him. I came home one afternoon early from work after there was a gun scare, and found him in bed with his secretary. I tossed him out on his ass right then and there. I filed for divorce and he fought me tooth and nail every step of the way, so it was dragged out in court for a year before it was finalized. I’ve been with exactly two people in the last twenty years, and I was miserable with both of them because they weren’t you.”

Cas was looking up at him, his expression full of amusement. “You know, for someone that always hated those chick flick moments you really outdid yourself.”

Dean laughed. “Yeah, I know. I’m a walking cliché, so sue me.” 

Cas’ expression became serious. “Dean, where are going from here? Are we just here for the night or…” He was almost afraid to ask for more than just this moment in time, though he knew he wanted an eternity with this man if the heavens would see fit to give him what he actually wanted for once. Dean leaned in and kissed him.

“I want so much more than just tonight.” Dean whispered, and Cas felt the icy grip of fear that had been squeezing his heart finally release, and he actually gasped with relief.

“Oh thank God, I thought you might just tell me to go away again!”

“Seriously? How could you even think that?” Dean asked.

“I don’t deserve you. I was cruel and selfish, and I don’t deserve you.” What pained Dean the most was hearing those words come from Cas’ mouth, and knowing he actually believed them.

“Cas, it’s all in the tense you choose to use. You were those things, but you’re not anymore. And I’ve never wanted anything more in my life than this, to have you in my arms, and to love you, knowing you loved me back.”

“I do Dean, I told you before that I love you, and I always have.” Cas grabbed the collar of Dean’s shirt and pulled him close, peppering his face with tiny kisses. “I love you Dean, I love you so damn much.” His words were as soft of a caress as his lips were and Dean melted into them.

“You won’t leave me again, will you?” Dean asked, his voice small, barely above a whisper as he tried to mask his fear. He couldn’t stand the thought of Cas ever leaving him again. It had damn near killed him the first time.

“Never, I’ll never leave you again.” Cas promised, and he meant it.

**Notes for the Chapter:**

> I decided to bypass the smut for this one. Sorry guys. We're almost to the end now. If you like it leave a kudos and a comment.


	16. The Morning After

**Summary for the Chapter:**

> The morning after the reunion when Dean asks Cas to stay.

Dean woke first to the sound of his phone vibrating somewhere nearby. He extricated himself from a sleeping Cas’ arms and followed the sound until he found his phone in the pocket of his jacket. He smiled when he opened the text.

Lexi: Hey dad, Uncle Bobby wants you and Cas to stop by today

Dean: How do you know Cas is still in town?

Lexi: Oh please, I’m not an idiot, he’s probably still asleep in your bed right now

Dean: I shall neither admit to nor deny that accusation

Lexi: So you’ll come?

Dean: I have to ask him

Lexi: Knew it

Dean: Shut up kid if you know what’s good for you

Lexi: So I take you guys kissed and made up?

Dean: There was kissing, but I’m not giving my kid details

Lexi: Good, I don’t want them. I just want you to be happy. Are you happy now?

Dean: More so than I think I’ve ever been

Lexi: That’s all I ask for. Uncle Bobby says be at the house in an hour

Dean: Aye aye captain

Lexi: Love you daddy

Dean: Love you princess. And thank you for talking to Cas yesterday

Lexi: Someone has to have your back

Dean: Well, I’m glad it’s you. See you later kiddo

Lexi: See you later 

Dean set the phone on the desk and went back to the bed, slipping back beneath the covers. Cas immediately cuddled closer.

“Is it morning already?” He grumbled, though he still hadn’t opened his eyes.

“Unfortunately, yes. It’s actually almost afternoon to be specific. Do you have to head back today?” Dean asked. Cas finally opened his eyes, blinking against the sunlight pouring into the room.

“No, why?”

“Well, we were invited to lunch at Bobby’s. And…I’m kind of staying til tomorrow. I was hoping you’d maybe stay with me?” Dean turned to look at him and Cas smiled.

“You want me to stay?” 

Dean nodded. “Yeah, I really do.” Cas kissed him softly before burying his face against Dean’s shoulder. “I’ll stay.”

Dean let out a sigh and turned so that he facing Cas. Waking up with this man in his arms was the most wonderful feeling in the world. It was one thing to just have him spending the night, sleeping on a pile of blankets on your floor when they were fourteen year old boys, but something completely different to be able to hold him and know that this man loved him, and that this could be something he woke up to every day for the rest of his life. He realized Cas was watching him.

“What are you thinking?” He asked.

“I was thinking about how I could get used to this, waking up with you in my arms.” Dean admitted and immediately felt embarrassed for saying it. He was just so comfortable with Cas, as though they hadn’t lost twenty years of their life at all. Cas kissed his shoulder and looked up at him again.

“I could get used to that too.” He said. Dean couldn’t help but smile, and it was so big it hurt his cheeks, but he couldn’t stop. God he loved this man, and he had nothing stopping him from admitting that to himself and to the rest of the world.

“Come on, we both need showers and I have to scrounge something up for us to wear to my uncle’s.” Dean kissed Cas softly on the forehead before getting up. Cas lay there for a minute watching Dean’s naked form as he made his way to the bathroom before he flipped onto his back and stretched. Last night had been amazing, and he was still trying to convince himself this was real, and that last night he had finally gotten his lifelong wish: Dean was his. Finally.

They left the Scion at the hotel and drove the ten minutes to Bobby and Ellen’s house where Lexi was waiting on the porch for them. To Dean’s surprise so was Connor. When they got out Dean took Cas’ hand and they met the kids on the porch.

“How did you get down here?” Dean asked his son.

“Mom let me borrow her car. Lex called me last night and said I should come down and see Uncle Bobby and Aunt Ellen. But she also kind of filled me in on things.” The boy replied with a smirk. He eyed Cas for a minute before offering his hand. 

“I’m Connor.” Cas shook his hand. “Nice to meet you Connor, I’m Cas.”

Connor raised an eyebrow and gave his dad a knowing smile. “So, you guys made up then.” Not a question at all. Dean didn’t bother acknowledging the comment.

“Where’s your aunt and uncle?” He asked instead. Lexi jerked a thumb towards the backyard.

“Uncle Bobby’s grilling. Aunt Ellen’s in the kitchen. Grandma and Grandpa are coming over too.” She added.

Dean smiled and shook his head. It wasn’t like most of his family didn’t already know Cas, because they did, and aside from his kids, they knew him rather well. But not like this, not as Dean’s…whatever he was. Dean wasn’t even sure what they were. Had they gone straight from childhood best friends to partners? That was something they would have to discuss later. For now he might consider the term ‘boyfriend’. It didn’t completely grate on his nerves to use it.

“Alexia Nicole Winchester, have you been talking to the whole family?” He chided.

She was smiling quite smugly at her dad. “Maybe I did.” Cas laughed. He liked Dean’s kids.

Dean tugged his hand. “Let’s go say hi to Ellen.” Cas followed him into the house and they went straight to the kitchen where they found Ellen stirring a fresh pot of iced tea. She dropped the spoon and hurried to give him a hug. He hugged her back and she turned to look at Cas with a cocky smile.

“Wasn’t sure we’d ever see your pretty face again. Good to see you Cas.” She pulled him into a hug and he gladly hugged her back. He had always loved Ellen, and Bobby too, despite his gruff exterior.

“Yes, well, I did a lot of groveling.” Cas admitted. “And I did a lot of forgiving.” Dean added.

“And I hope you were both honest with one another.” She said, looking at each of them sternly.

“We were more honest last night with each other than we were in the four years that we practically lived in each other’s homes.” Cas said. Ellen’s expression softened and she smiled. “Good, cause you boys, you belong together. I’m just glad you both finally got your heads out of your asses.” Cas snickered at that and Dean elbowed him playfully. 

The sound of another car pulling into the driveway drew Dean’s attention and he went back out to the porch. His dad had just pulled into the driveway and his mother was already on the porch hugging each of the kids. She grabbed Dean when she saw him and hugged him too. 

“Where is he?” Mary Winchester asked.

“Who mom?” Dean asked innocently. Mary frowned and looked uncertainly at her granddaughter. “Isn’t Cas here?”

Dean grinned and turned to find Cas was standing just inside the doorway. He took his hand and pulled him back out onto the porch. Mary’s face lit up at the sight of him and she pulled him into a hug. Her husband John had just climbed the steps and he smiled wide at the sight of Cas.

“You grew son.” He commented. Cas smiled. “Yes sir, I did.” John gave him a quick hug. “We missed having you around. Dean wasn’t the same without you.” 

Cas looked over at Dean and smiled before looking back at John. “I wasn’t doing so well either.” “Well, glad you two made up and figured out that you were in love with each other. Hell, even we knew it back then. And don’t think I didn’t know about that boyfriend you had junior year. You two weren’t so good at hiding things. But you were even worse at hiding the puppy dog eyes you got every time you looked at Cas here, and he was just as bad. I still don’t know how you two didn’t figure it out back then.” John said with a huffed laugh.

Dean threw his hands up in mock exasperation. “How did everyone figure this out, but no one thought to let us in on it?!”

“I believe they were hoping we’d overlook our preconceived notions of one another and just admit how we felt.” Cas said.

“Yeah, well, we were teenage boys. We weren’t that smart.” Dean complained. Cas put his arms around Dean’s waist and smiled at him. “Good thing we’re not teenagers anymore.” Dean put his arms around Cas and laughed. “Damn good thing we’re not!”

John and Dean disappeared into the yard to help Bobby with the grilling while Mary, Ellen, and Lexi sat in the kitchen with Cas. Mary wanted to know what he had been up to, and what the hell had happened between him and Dean for them to have that terrible falling out. He carefully explained everything, just as he had done last night with Dean, and he was relieved to see sympathy instead of anger on her face. It would have crushed him for her to be angry with him still after all these years. The Winchesters had always been more of a family to him than his own had been.

“So, are you and my dad like…together now?” Lexi asked.

Cas wasn’t exactly sure how to answer that. He wanted to say yes, absolutely! But he and Dean hadn’t exactly said that. He was just opening his mouth to answer when Dean walked in the room.

“Dad, are you and Cas a couple now?” She redirected the question at him since Cas wasn’t answering her fast enough. He set the plate of burgers he was carrying on the counter and looked over at Cas. There was so much love there that it made Dean’s heart swell just to see it. He nodded.

“Yeah, we are.” The smile that rose up on Cas’ face was by far the most beautiful one he had ever seen. Lexi was practically beaming. “Good, I’m glad.”

Cas turned to look at her and the surprise that was written all over his face amused her. “You are?” She nodded. “You make my dad happy. He hasn’t been happy in a really, really long time, so yeah, I’m glad you two have each other. I think he makes you just as happy.” Cas blushed and lowered his eyes to his hands which were fidgeting in his lap. “Yes he does.” 

Bobby walked in with John and more trays of food, and he actually smiled when he saw Cas sitting at the table. “It’s about damn time we saw you around here again.” Cas was practically beaming. “I’m glad to be back.” And that was the truth. Cas had always felt more at home in the Winchester house or even at Bobby’s than he had ever felt at home. This felt like coming home again, and it was wonderful.

**Notes for the Chapter:**

> One more chapter after this and we're all done. I hope you're enjoying this. If you like it leave a kudos and a comment.


	17. A Lifetime of Love

**Summary for the Chapter:**

> Cas and Dean prepare to spend the rest of their lives together.

Chicago June 2016

“Dad! Hurry up or we’ll be late!” Connor was yelling from the living room.

“I’m trying to hurry! Let me get my damn shoes on!” He yelled back. Damn it if he was going to be rushed. Lexi appeared in the doorway. “Dad, we have twenty minutes to get there and you don’t even have your shoes on!” She moved over to where he was sitting on the bed and ran her fingers through his hair to move the part from the middle. He pushed her hand away and stood up. “Shoes are on now, happy?” She smiled cheekily. “Yes I am, so let’s get going.”

Lexi was driving, he was too nervous. It was only a five minute drive but it was the longest five minutes of his life. Connor leaned forward from his seat in the back of the Impala as Lexi found a parking spot and patted his dad on the shoulder. “Last time you’ll ever have to do this dad. Relax, it’ll be over soon.” Dean gave a nod and opened the car door. His mom was standing on the steps smiling and waiting for him. As he approached her smile grew wider and she pulled him into a hug. 

“Oh baby, you are so handsome! Are you ready?” She asked as she pulled back to look at him. He nodded. “Absolutely.” He offered her his arm and they stepped inside. Ellen and his aunts Doris and Lynn were also waiting with huge smiles on their faces.

“Look how handsome you are.” Doris gushed and lightly pinched his cheek. “He’s gorgeous. Can’t wait to see the other one.” Lynn was saying as she straightened his collar.

“Oh ladies, that’s enough fussing, ok?” He couldn’t be angry with them though, he was too excited. Mary checked her watch. “Get ready. Get to your seats everyone!” She turned to her son. “Are you ready to get married honey?” He smiled and nodded. “Yes I am.”

They had chosen a church at Cas’ insistence. He wasn’t overly religious, especially after having it shoved down his throat his entire childhood, but he had wanted a church wedding, and Dean was loathe to deny him this one little thing. When he’d married Scott it had been at city hall, and with very little fanfare. This time around the church was filled with all of the people he loved most. Charlie was waiting already at the altar with his brother. Since Sam was performing the ceremony Charlie was acting as Dean’s best man. Benny was right behind her. Cas was waiting, that beautiful smile that Dean was certain he would never grow tired of on his face as he looked up and saw Dean making his way down the aisle with Mary. This was absolutely the best decision he had ever made. Reconnecting with Cas was like reconnecting with the other half of his soul, and they had spent very little time apart in the last year. Cas had moved in six months ago and proposed a month after that. Dean had always prided himself on his masculinity and the way he took charge in all aspects of his life, but when it came to Cas he was more than willing to let him take the lead. They were happier than they had ever been and Dean knew this was forever. Nothing would tear them apart ever again. 

At the altar Mary paused to kiss him on the cheek before moving to her front row seat next to John. Dean glanced over at his dad who was smiling up at him with tears in his eyes. He nodded and Dean gave a soft nod back. When he climbed the two short steps to stand in front of Cas all nervousness that he had been feeling faded away. Cas reached out and took his hand, and he squeezed it, offering a smile of his own. Sam cleared his throat and Dean looked up at his little brother. Sam was smiling almost as big as he was, and it gave him great joy to know that his family fully supported his relationship with Cas, and that they supported their marriage. Sam began the ceremony, reciting the words that bind Dean to Cas for the rest of their lives, and unlike his first marriage which had been filled with doubt and worry, he was now filled with nothing but love and hope for their future together. Cas had changed, just as he’d said, and grown to become the most patient, thoughtful, and caring man Dean could have ever hoped for. Long gone were his selfish tendencies, and Cas made sure every single day that Dean knew how loved and appreciated he was. Dean knew he would love this man for the rest of his life.

When the ceremony was over and the rings had been exchanged Dean leaned in to kiss his husband and the entire church applauded. Cas was smiling and Dean pulled him in for another kiss. This was the beginning of the rest of their lives, and neither man could wait to get started.

**Notes for the Chapter:**

> This is the last chapter. I hope you all enjoyed it. If I turn it into a book there will be WAY more detail, and way more emotion. If you like it leave a kudos and a comment, I greatly appreciate it. Thanks for reading!

**Author's Note:**

> If you like this, leave kudos and comments. I'm considering taking this one, adding a ton more detail (including way more flashbacks) and turning it into a full fledged book. Let me know what you think.


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